Phenylhydrazine → 1-phenyl-3-(thiophen-2-yl)-1H-pyrazol-5-amine

HRID 628782

Reaktionsgleichung

Reaktionsgleichung von HRID 628782
[C:1]1([NH:7][NH2:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O=[C:10]([C:14]1[S:15][CH:16]=[CH:17][CH:18]=1)[CH2:11][C:12]#[N:13]>CO>[C:1]1([N:7]2[C:12]([NH2:13])=[CH:11][C:10]([C:14]3[S:15][CH:16]=[CH:17][CH:18]=3)=[N:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Komponenten

4

Edukt 2

HCID 7516PhenylhydrazineHCID 1418532-Thenoylacetonitrile

Produkt 1

HCID 162286411-phenyl-3-(thiophen-2-yl)-1H-pyrazol-5-amineAusbeute 98,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

Phenyl hydrazine (143 mg, 1.32 mmol) and 3-oxo-3-(2-thienyl)propionitrile (200 mg, 1.32 mmol) were placed in a microwave vial and dissolved in methanol (660 μL). The vial was sealed, placed in a microwave oven and heated at 120° C. for 40 minutes. After this period, the reaction mixture was concentrated to dryness in vacuo. The residue was redissolved in ethyl acetate and the organic solution washed with water, saturated aqueous NaHCO3 and brine, respectively. The organic layer was dried over anhydrous Na2SO4 and concentrated. The crude material was purified by flash chromatography (20-50% ethyl acetate/hexanes gradient) to afford the desired intermediate, 2-phenyl-5-thiophen-2-yl-2H-pyrazol-3-ylamine (315 mg).

Aufarbeitung

  1. customThe vial was sealed
  2. customplaced in a microwave oven
  3. waitAfter this period
  4. concentrationthe reaction mixture was concentrated to dryness in vacuo
  5. dissolutionThe residue was redissolved in ethyl acetate
  6. washthe organic solution washed with water, saturated aqueous NaHCO3 and brine
  7. dry with materialThe organic layer was dried over anhydrous Na2SO4
  8. concentrationconcentrated
  9. customThe crude material was purified by flash chromatography (20-50% ethyl acetate/hexanes gradient)

Quellen und Nachweise

ORD-Eintrag
ord-02fc0c477ed3473c8eb9ced534253850
Quelldatensatz
uspto-grants-2016_04
Patentnummer
US09315449B2

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